Ok thanks, a mod just confirmed that the dress scene is indeed random, too bad now I will have to keep skipping weeks to try and see.
The anniversary has a whole plotline, I recommend checking it out, its good. Josef needs to be kicked out otherwise nothing will happen on that day (other than maybe total Adrian sharing). As the mod said the particular pic is not in the game yet and told me to delete, but there are 5 or so and dialogue.
I know, if you go the beer route it feels quite harsh the way you kick him out, felt sorry for the dude. Maybe try the Isabella one where you bang his ex together with him, this way you can make him leave as well. If you prefer, this can probably be done before you have actual sex with Anna so he "cheated" first and its more justified. But def recommend another save for solo path